This group soon lost its less-dedicated members and the remaining quartet, also featuring Henk Lodema, Geert van Driesten, and Rob Lodema, embarked on a tour of Great Britain, this time under the name of the Hollander Boys, something which had been cooked up by the English comedian Tom Moss. At the end of this tour, employment fell off completely and Geldray went on his own, trying out the scene in nearby Belgium where he finally landed an engagement of more than a year at a club called Le Boeuf sur la Toit (in English, this means, "the Bull on the Roof"). His old friend, bandleader Johnny Fresco, who perhaps might have had a more appropriate career as a painter, offered the harmonica player a job with his dance band back home in Den Haag, representing the first time that Geldray had the opportunity to play in front of a Dutch audience. The bandleader Ray Ventura became another important contact, offering Geldray connections in jazz-crazy Paris. Geldray performed with the Ray Ventura Orchestra until the outbreak of the Second World War. In early 1938, Geldray met the great French jazz guitarist Django Reinhardt, beginning a friendship and musical collaboration that lasted until early 1940. One of the strangest aspects of this relationship is a record released by Reinhardt and harmonica virtuoso Larry Adler, on which the harmonica player is actually Geldray, not Adler.
During the height of his relationship with Reinhardt, Geldray had no choice but to pack up his harmonicas and flee, due to one big problem: he was Jewish. He wound up in Liverpool, and by 1942 had become well-liked by the powers at the BBC. The sound of his harmonica became one of the few soothing sounds in wartime Britain. Accompanied by pianist Ben de Koning, Geldray even enjoyed royal invitations such as performing at a special party for the Princess. Enlisting in the army, the heroic Geldray was wounded during the landing at Normandy. In 1945, he was finally able to return to Amsterdam, where he found that his family had disappeared. Both his parents and younger sister had been executed by the Nazis. His desire to stay in Holland dissipated by this tragedy, he went back to work with Ventura for two years before returning to England. His involvement with the Goons began thereafter, starting with the earliest versions of the show in 1951 and lasting until the final real broadcast in early 1960.
Following a period of freelancing, including a return to the group of Fresco, he began playing as part of the combo on the Queen Elizabeth ocean liner. His next stop was Los Angeles, beginning a period of musical opportunities in America. He played with jazz and vocal greats such as Sarah Vaughan, Dinah Shore, and Billy Daniels. Despite this success, he began drifting out of music professionally, beginning a family and settling in the San Fernando Valley where he began working in a department store as a clothing salesman. He relocated two years later to Boston, working for the Christian Science Monitor as a regional sales supervisor. Within a few years he would be performing again, this time on the occasion of a Goon Show reunion that was part of the 50th anniversary of the BBC. Upon returning to the United States, Geldray became involved in a group called the Blow Hards that lasted for some nine years. His next admirable professional move was to join the care staff at the Betty Ford Cancer Treatment Institute. In 1995, just short of 80 years old, Geldray performed for the Dutch Harmonica Festival in Rotterdam, but was advised by a physician to stop working full-time the following year. He retired to Palm Springs, CA. Producer George Martin helped create several memorable tracks featuring the harmonica soloist, most notably a superb version of Crazy Rhythm. ~ Eugene Chadbourne, Rovi